Illustrator cs5 won't return to previous file

Have new iMac with Sierra. Have posted before wondering whether cs5 worked in Sierra. It does but have one problem. When working on Illustrator document, after placing jpg, when hitting PLACE again the window opens to same old file I went to a month ago instead of the same file. Same problem when I try to open another document after opening a previous one in Illustrator. Goes to the same old file. Not a problem in Photoshop or InDesign. Never had this problem before with Illustrator cs5 on other computers with other operating systems.

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-Which version of macOS Sierra - 10.12.6?
-Is it Illustrator CS5 (15/15.0.1/15.0.2)?
-Did you perform a migration from the old Mac to the new one, or did you get CS5 to somehow install in Sierra from scratch?
-Can you upload a screenshot of what you see when the issue occurs?

I understand that most functions may work, but since CS5 was released 8 years ago, for versions of OS X released almost 9 years ago, there will definitely be some incompatibilities/issues.

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-Which version of macOS Sierra - 10.12.6?
-Is it Illustrator CS5 (15/15.0.1/15.0.2)?
-Did you perform a migration from the old Mac to the new one, or did you get CS5 to somehow install in Sierra from scratch?
-Can you upload a screenshot of what you see when the issue occurs?

I understand that most functions may work, but since CS5 was released 8 years ago, for versions of OS X released almost 9 years ago, there will definitely be some incompatibilities/issues.

- Bought new computer with Sierra 10.12.6.
- Illustrator cs5 15.0.0
- Installed from original CD. Had to work with Adobe tech to install because cs5 was older than permitted.
- Uploaded screen shot showing placement of photo from a folder and the folder window that came up when I hit PLACE again. Keeps going to this folder rather than the folder previously placed from. NOTE: Keeps going to Documents folder
now. Last week it kept going to a different folder.

If you want to try it, here is a link to the Adobe Illustrator 15.0.2 Update. Not sure if it will install under Sierra, or if it will correct the issue you are having. Just thought I would let you know.

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